1. Field of the Invention
This invention relates to novel 1-phenethylimidazoles substituted at the position .beta. to the imidazole ring by a hydrocarbyl ester or a hydrocarbyl mono- or dithioester the use of these imidazoles as antimicrobial agents, the combination of these imidazoles with a suitable carrier, the preparation of these imidazoles, and the use of these imidazoles as intermediates in the preparation of 1-[.beta.-(R-thio)phenethyl]-imidazoles.
2. Prior Art
It is generally known in the art that certain 1-(.beta.-aryl)ethylimidazole ethers and amines have anti-fungal and anti-bacterial activity. See, for example, U.S. Pat. Nos. 3,717,655 and 3,839,574, both to Godefroi and Heeres and U.S. Pat. No. 3,658,813 to Godefroi and Schuermans. Representative of the ethers is the compound miconazole nitrate having the formula ##STR1## the active ingredient in Monistat.sup.R Cream sold by Ortho Pharmaceutical Co. Other 1-ethylimidazoles which are known include those disclosed in U.S. Pat. Nos. 3,796,704 and 3,892,764 to Metzger et al and U.S. Pat. No. 3,914,427 to Kramer et al. These, too, show anti-fungal activity.
An entirely new class of 1-[.beta.-substituted phenethyl]-imidazoles has now been discovered which shows very good anti-fungal and anti-bacterial activity as well as antiprotozoal activity. These are the 1-phenethylimidazoles which are substituted at the position .beta. to the imidazole with an ester or mono- or di-thioester moiety. The existence of related compounds such as (1,1-diphenyl-2-acetoxyethyl)imidazole or 1-(1-phenyl-1-t-butyl-2-acetoxyethyl)imidazole was disclosed in the broad disclosure U.S. Pat. No. 3,892,764, but, the compounds of the instant invention are chemically different and appear to be superior to the compounds of the 3,892,764 patent.